Indoles Oxidative Ring-Opening/Cyclization Cascade with the 1,2-Diaminoarenes: Direct Synthesis of 2-Aryl-3-(2-aminoaryl)quinoxalines.

A mild oxidative sequential tandem reaction was developed to rapidly generate 2-aryl-3-(2-aminoaryl) quinoxalines. This method exploited 2-substituted indoles as substrate to form quinoxalines in a one-pot reaction. The key to this tandem reaction was the formation of 3-iodoindoles, which underwent Kornblum-type oxidation with DMSO to generate active imine 2-substitued 3H-indol-3-ones. The active imines were captured in situ by 1,2-diaminobenzenes to construct diverse quinoxalines. The transformation can be accomplished at room temperature with excellent functional group tolerance.

Citation

Jianwei Yan, Linxia Zheng, Jiangfei Wang, Xiaomin Liu, Youhong Hu. Indoles Oxidative Ring-Opening/Cyclization Cascade with the 1,2-Diaminoarenes: Direct Synthesis of 2-Aryl-3-(2-aminoaryl)quinoxalines. The Journal of organic chemistry. 2022 May 06;87(9):6347-6351

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PMID: 35420817

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